I just got a Blackberry Curve 8300 and am attempting to sync it with my new MacBook 10.4.10 through the PocketMac program. Specifically, when I select a 2-way transfer for my calendar, the items on my Mac iCal show up on my Blackberry, but not the other way around. I called some support people, but they have no idea what PocketMac is!

Depending on how you manage your contacts, i.e. entourage, address book.. in pocket mac click blackberry>contacts> then check the box to sync contacts and then choose whichever program you use and go to advanced options and set a rule in there for your handset to win on conflicts..

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I just got a Blackberry Curve 8300 and am attempting to sync it with my new MacBook 10.4.10 through the PocketMac program. Specifically, when I select a 2-way transfer for my calendar, the items on my Mac iCal show up on my Blackberry, but not the other way around. I called some support people, but they have no idea what PocketMac is!

After testing and using various solutions, I'd have to recommend just buying the Missing Sync. It's worth the loot to know my calendars and contacts are going to sync correctly everytime. I never had any luck with PocketMac and booting into Windows via Fusion (or Parallels if you're using that, though fusion is much better) is a bit of a hassle just to sync. I'm hoping Plaxo will soon support OTA syncing, that'd be ideal for me. I sync to my Mac via Missing Sync and then Plaxo resident syncs up to my Plaxo account now, cutting out that middle step would be great.

I am actually having a lot of problems syncing ical right now to missing sync but in regard to your issue, RIM had me download a calendar patch that is supoosed to fix the problem of the BB not overwriting ical events. You can have them send it to your device. I do not have a data plan on my curve so I went on my friend's pc and downloaded the desktop manager first then installed the calendar patch that way (all on their site).

So far, I can't sync so not sure if switching to pocketmac is the answer but they have 24/7 customer support and I suggest you call them really early in the morning eastern time if you want to have them send the patch to you: 1877 255 2377